Largazole

Base Information

• Chemical Name: Largazole
• CAS No.: 1009815-87-5
• Molecular Formula: C29H42N4O5S3
• Molecular Weight: 622.874
• Mol file: 1009815-87-5.mol

Synonyms:Largazole

Chemical Property of Largazole

Chemical Property:

• PKA: 12.12±0.70(Predicted)
• PSA: 212.64000
• Density: 1.317 g/cm³
• LogP: 5.02170
• Storage Temp.: Storage at -20℃

Purity/Quality:

99% ^*data from raw suppliers

Largazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Largazole is derived from cyanobacteria that grow on coral reefs, which may have potentials as an anti-cancer drug. Largazole is a potent histone deacetylase inhibitor. [1] Largazole has its potent antiproliferative activity against a number of cancer cell-lines including MDA-MB-231 mammary cells (GI50 7.7 nM), U2OS fibroblastic osteosarcoma cells (GI50 55 nM), HT29 colon cells (GI50 12 nM), and IMR-32 neuroblastoma cells (GI50 16 nM). Largazole is a potent and selective histone deacetylase (HDAC) inhibitor.

Technology Process of Largazole

There total 57 articles about Largazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

Largazole thiol (1033814-08-2) + n-octanoic acid chloride (111-64-8) → largazole (1009815-87-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ja8033763

Reference yield: 43.0%

C58H64N4O8S3 (1263375-82-1) → largazole (1009815-87-5) + 2-epi-largazole (1196806-45-7)

Guidance literature:

C₅₈H₆₄N₄O₈S₃; With diethylamine; In dichloromethane; at 20 - 25 ℃; for 3h; Inert atmosphere;

With 1-hydroxy-7-azabenzotriazole; N-ethyl-N,N-diisopropylamine; HATU; In acetonitrile; at 20 - 25 ℃; for 12h; Inert atmosphere;

DOI:10.1055/s-0029-1216931

Reference yield: 42.0%

octanethioic S-acid (7530-92-9) + (5R,8S,11S)-11-((E)-4-chlorobut-1-en-1-yl)-8-isopropyl-5-methyl-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-triene-6,9,13-trione → largazole (1009815-87-5)

Guidance literature:

With potassium carbonate; potassium iodide; In acetonitrile; at 25 ℃; for 16h; Inert atmosphere;

upstream raw materials:

S-but-3-enyl octanethionate

C₁₉H₂₄N₄O₄S₂

Largazole thiol

n-octanoic acid chloride

Downstream raw materials:

D-Val-OH

L-valine

(S)-Malic acid

D(S)-2-methylcysteic acid

Refernces

• 1、 Ren, Qi,Dai, Lu,Zhang, Hui,Tan, Wenfei,Xu, Zhengshuang,Ye, Tao. "Total synthesis of largazole". . p. 2379 - 2383. Retrieved 2008.
• 2、 Nasveschuk, Christopher G.,Ungermannova, Dana,Liu, Xuedong,Phillips, Andrew J.. "A concise total synthesis of largazole, solution structure, and some preliminary structure activity relationships". . p. 3595 - 3598. Retrieved 2008.
• 3、 Ying, Yongcheng,Taori, Kanchan,Kim, Hyoungsu,Hong, Jiyong,Luesch, Hendrik. "Total synthesis and molecular target of largazole, a histone deacetylase inhibitor". . p. 8455 - 8459. Retrieved 2008.
• 4、 -. "METHOD FOR PREPARING LARGAZOLE ANALOGS AND USES THEREOF". Paragraph 00156; 00163. . Retrieved 2016/09/26.
• 5、 Benelkebir, Hanae,Marie, Sabrina,Hayden, Annette L.,Lyle, Jason,Loadman, Paul M.,Crabb, Simon J.,Packham, Graham,Ganesan. "Total synthesis of largazole and analogues: HDAC inhibition, antiproliferative activity and metabolic stability". supporting information; experimental part. p. 3650 - 3658. Retrieved 2011/08/03.